methyl 1-[5-O-(diethoxyphosphinyl)methyl-2,3-O-isopropylidene-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxylate | 594860-44-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: methyl 1-[5-O-(diethoxyphosphinyl)methyl-2,3-O-isopropylidene-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxylate
• 英文别名: Methyl 1-[5-O-[(diethoxyphosphinyl)methyl]-2,3-O-(1-methylethylidene)-I(2)-D-ribofuranosyl]-1H-1,2,4-triazole-3-carboxylate；methyl 1-[(3aR,4R,6R,6aR)-6-(diethoxyphosphorylmethoxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2,4-triazole-3-carboxylate
• CAS: 594860-44-3
• 化学式: C₁₇H₂₈N₃O₉P
• 分子量: 449.398
• InChiKey: HEIKUNWZUPBVHY-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  129.46
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 1-[5-O-(diethoxyphosphinyl)methyl-2,3-O-isopropylidene-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 生成 1-[(3aR,4R,6R,6aR)-6-(diethoxyphosphorylmethoxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases

  摘要：

  IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5'-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not assured, and usually is inefficient. In order to bypass cellular phosphorylation, a series of azole nucleoside 5'-MP mimics (P1Ms) based on ribavirin, EICAR and bredinin were synthesized and screened against human and C. albicans IMP dehydrogenises. P1Ms 8, 16, 25, 28 and 29 demonstrated substantial IMPDH inhibition with K-i values in low micromolar range.

  DOI：

  10.1081/ncn-120027838
• 作为产物：
  描述：

  三乙酰利巴韦林甲酯 在 高氯酸 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 6.0h， 生成 methyl 1-[5-O-(diethoxyphosphinyl)methyl-2,3-O-isopropylidene-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases

  摘要：

  IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5'-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not assured, and usually is inefficient. In order to bypass cellular phosphorylation, a series of azole nucleoside 5'-MP mimics (P1Ms) based on ribavirin, EICAR and bredinin were synthesized and screened against human and C. albicans IMP dehydrogenises. P1Ms 8, 16, 25, 28 and 29 demonstrated substantial IMPDH inhibition with K-i values in low micromolar range.

  DOI：

  10.1081/ncn-120027838